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Title: Lupane derivatives from Lophopetalum wallichii with farnesyl protein transferase inhibitory activity
Authors: Sonja Sturm
Roberto R. Gil
Hee Byung Chai
Olipa D. Ngassapa
Thawatchai Santisuk
Vichai Reutrakul
Anne Howe
Marcia Moss
Jeffrey M. Besterman
Shi Lin Yang
John E. Farthing
R. Murray Tait
Jane A. Lewis
Melanie J. O'Neill
Norman R. Farnsworth
Geoffrey A. Cordell
John M. Pezzuto
A. Douglas Kinghorn
University of Illinois at Chicago
The Forest Herbarium, Thailand Ministry of Natural Resources and Environment
Mahidol University
GlaxoSmithKline, USA
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry;Medicine;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 1-Jul-1996
Citation: Journal of Natural Products. Vol.59, No.7 (1996), 658-663
Abstract: Chloroform-soluble extracts of the stems and of the mixed stems and stem bark of Lophopetalum wallichii were found to be inhibitory in a farnesyl protein transferase (FPTase) bioassay system. During the course of activity- guided fractionation, the known lupane-type triterpenes, ochraceolide A (1), ochraceolide B (2), betulin, and lupeol and the new lupane lactone, dihydro ochraceolide A (4), were isolated. The stereochemistry of the epoxide group of ochraceolide B (2) was determined by preparation of both epoxide isomers [2, and the new semisynthetic derivative, 20-epi-ochraceolide B (3)] from 1. The structure of 4 was established by reduction of 1 with sodium borohydride. Compounds 1 and 2 exhibited significant inhibitory activity in the FPTase assay (IC50values of 1.0 and 0.7 μg/mL, respectively). Lupeol was found to be weakly active (IC5065.0 μg/mL) in this test system, whereas no significant inhibition was detected for betulin or compounds 3 or 4. When evaluated against a panel of human cancer cells in culture, compounds 1 and 4 were modestly cytotoxic. Compounds 2 and 3 were not active in the panel.
ISSN: 01633864
Appears in Collections:Scopus 1991-2000

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